Study of solid state reactions has led to an improved knowledge of reaction dynamics (e.g., the effect of orientation on rearrangements and cycloaddition reactions). In addition solid state organic reactions are used for industrial syntheses and are the process by which solid drugs degrade. A consideration of the literature shows that no extensive studies of solid state oxidation reactions have been carried out even though these reactions are widespread. In addition, several known solid state oxidations are more specific than their solution counterparts (e.g., stilbene ozonolysis). Based on these encouraging reports we plan to begin a major study of solid state oxidation reactions. In the first years of this project we plan to study the relationship between loss of solvent of crystallization, crystal packing and solid state oxidation by studying the reactions of steroids, rubrene and derivatives, dialuric acid, phorbol, and the reduction of (HN4)2C2O4.H2O2 to (NH4)2C2O4.H2O. We also plan to try to develop an absolute asymmetric synthesis based on solid state oxidation reactions. Several polycyclic aromatic hydrocarbons while not optically active crystallize in chiral crystals. Oxidation of a single chiral crystal could in principle lead to the formation of optically active products if oxygen reacts from only one side of the crystal or from one side of the hydrocarbon. Such a reaction could be of synthetic and evolutionary significance. The existence of an absolute asymmetric reaction could suggest a mechanism for the generation of optical activity from optically inactive starting materials. In addition a knowledge of the structure of the products of the solid state oxidation of polycyclic aromatic hydrocarbons might have implications in the area of the toxicological danger of these products. The significance of other studies proposed in this application may lie in the following areas: (1) Developing more specific syntheses; (2) Stabilizing drugs by rational approaches; (3) Developing an understanding of the general mechanisms of solid state oxidation reactions; and (4) Improving our knowledge of reaction dynamics.